Reaktion #171499

Reaktionsgleichung

(8-Bromo-octyl)-benzene

3-picoline

→

product

Ausbeute 76.0%

3-methyl-1-(8-phenyl-octyl)-pyridinium bromide

Ausbeute 76.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution refluxed for 24 hours
2. 2
   SonstigeThe acetonitrile was removed in a vacuum
3. 3
   Sonstigethe resulting residue was partitioned between ether and water
4. 4
   WaschenThe aqueous layer was washed extensively with ether until no picoline
5. 5
   workup.WAITwas left in the aqueous layer
6. 6
   ExtraktionThe resulting aqueous solution of the product was extracted with chloroform
7. 7
   SonstigeThe chloroform was removed

Vorschrift

(8-Bromo-octyl)-benzene (1 mmol) was added to a solution of 3-picoline (3 mmol) in acetonitrile, and the solution refluxed for 24 hours. The acetonitrile was removed in a vacuum and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no picoline was left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (76%). 1HNMR (300 MHz, CDCl3, ppm) 9.40 (s, 1H), 9.22 (d, 1H), 8.02 (d, 1H), 7.96 (dd, 1H), 7.12-7.22 (dd, 4H), 4.94 (t, 2H), 2.62 (s, 3H), 2.56 (t, 2H), 1.94-2.04 (m, 2H), 1.50-1.60 (m, 2H), 1.20-1.40 (br, 8H). 13CNMR, 145.68, 144.65, 142.87, 142.37, 139.79, 128.55, 128.40, 127.89, 125.76, 62.20, 36.19, 32.29, 31.73, 29.53, 29.44, 29.33, 26.40, 19.11.

Quelle